


Moving Your Body So Brave And So Free

by jackles67



Series: The Skirt Thing [1]
Category: Supernatural
Genre: Crossdressing, M/M
Language: English
Status: Completed
Published: 2013-06-12
Updated: 2013-06-12
Packaged: 2017-12-14 19:36:30
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,645
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/840589
Author URL: https://archiveofourown.org/users/jackles67/pseuds/jackles67
Summary: <blockquote class="userstuff">
              <p>Dean finds a skirt in Sam's bag and Sam wears it for him.</p>
            </blockquote>





	Moving Your Body So Brave And So Free

**Author's Note:**

  * For [littleredcup](https://archiveofourown.org/users/littleredcup/gifts).



> unbetaed.

Dean’s torn between pride and disbelief - his little brother got laid and the first he hears of it is finding the girl’s clothes - which, by the way,  _nice -_ in Sam’s duffel when he’s looking for a sweatshirt. The anticipation of Sam’s annoyed “Deeeaaann” tips the balance and Dean stuffs the skirt into his own bag before stuffing himself down into a corner of the couch to watch fuzzy tv while the space heater croaks out a thin stream of hot air and the smell of burnt carpet. They better go somewhere warm next. Florida. Texas. Fucking Arizona, whatever. 

Sam comes home late and Dean had a whole thing planned, he was going to tease the every-loving shit out of Sam, make him turn tomato red and maybe even wrestle like they never seem to do anymore, but he clearly underestimated his own sense of betrayal. 

“You had sex?” Dean’s a smooth guy. This is not smooth. This is an awkward, stilted question that, for what it’s worth, has Sam blushing furiously behind his too-long hair. 

“No, Dean. Told you I’d tell you all about it when it happens.”

“Then why do you have chick clothes in your bag?”

Sam’s eyes fly to the still-open duffel sitting on his bed and his mouth is opening and closing but nothing’s coming out. Dean suddenly doesn’t want to know, doesn’t like anything that leaves Sam, of all the snot-nosed know it all loud mouths, speechless. He’s opening his mouth to apologize when Sam whirls around to glare down at him and the anger written into every line of his face twists it up, turns it into something Dean doesn’t often have aimed at him. He’s kind of scared - Sam’s smaller but he’s fucking ruthless when he fights for real. 

“Don’t you  _ever_ go through my shit again, Dean.”

And that’s that. 

***

That’s that until it hits Dean, something like 36 hours later, that the skirt might have been Sam’s. Like,  _Sam’s_. 

“Oh,” Dean breathes, turning wide eyes on Sam, who’s staring out the window of the Impala, cheek pressed to the glass. He’s still angry - Dean knows Sam can hold a grudge like fucking no one else, just hasn’t had it held against him yet, or at least not like this. Dean doesn’t know how to deal with it so he’s acting like everything’s fine, trying not to wince when Sam throws him dirty looks every few minutes. “You wear it?”

Sam doesn’t startle, doesn’t need any kind of context to that statement, just stares out the window for a moment before answering. 

“Seriously? A day and a half to reach that conclusion? 

“Really? I’m a freak in every other aspect of my life, why not in this one?” It sounds like a well-rehearsed line, like something Sam tells himself to make it okay. Dean laughs. 

“Dude, wearing a skirt does not qualify you as  _freaky._ I’ve seen some - “

“Not making me feel better, Dean.”

“What about the people you wear it for? They must like it, right? They call you a freak?” It occurs to Dean, belatedly, that the answer might be ‘yes’. 

“I don’t wear it for anyone else.” Sam sounds scandalized by the idea and Dean wants to laugh. 

“C’mon, you don’t want someone tellin’ you how pretty you look in that thing?” It’s mostly a joke but he’s curious too. It’s a nice skirt, pleated on one side, some pink and orange color like salmon. Coral? Something like that. Dean still has it, which is weird but not as weird as trying to give it back would be. 

This time Sam keeps quiet and Dean sneaks a look over at him. He’s  _blushing_ , like, hard. His eyes are fixed on a spot in the middle distance, staring straight out the window, head tilted to keep his bangs in his face but Dean can see the angle of his cheekbone, a strip of tanned neck and both are red like a bad sunburn.  

“Dude.” This has to be the weirdest thing be giving advice to your kid brother about. “There’s nothing wrong with your skirt and there’s nothing wrong with having someone tell you what a pretty girl you are while you wear the damn thing.”

“Boy.” 

“Huh?” Dean’s eyes are back on the road but he can feel Sam watching him, steady and intense like he does sometimes. 

“I want someone to tell me what a pretty  _boy_ I am.” It’s a confession, whispered and all and Dean feels like this is the part where he should laugh, tell Sam it’s fine, tell Sam there are probably thousands of people just waiting to be offered the chance to do just that - except now he’s imagining the trucker they just passed, or that lady who served them coffee at the diner, or the girl two years older than Sam who watched him for the entire three weeks they were at their last school, sitting on their bed in a crappy motel room and telling Sam how good he looks. 

See, Sam gets his need to prove himself fulfilled by school, gets his need to rail and fight fulfilled by Dad, and from what Dean can tell, he gets whatever needs his teenage hormones have pumping through his body fulfilled by his right hand. Everything else, Dean takes care of. Dean doesn’t know what the hell kind of need this qualifies as, but fuck if some stranger’s gonna be the one giving it to Sam. 

“I could do that.” Dean’s voice comes out rough and too serious, all traces of humor wiped away by twisting uncertainty in his belly. 

“You could - “

“I mean, I bet you do, Sam. I bet you look real good in that little skirt, always had real long legs.”

This is the part where Sam should tell Dean to shut up, tell him to shut the hell up and never mention the skirt again, tell him he sounds like an idiot and this isn’t what Sam meant and he doesn’t want it from Dean anyway. Sam’s silent, still staring out at the fields that haven’t changed for hours, still blushing. 

“We could try it. See if it’s… see if that’s what you…”

Sam jerks his head, enough of  a nod to settle the snakes in Dean’s stomach for all of five seconds before it hits him that he just offered to watch his little brother wear a skirt and tell him how good he looks in it. At least he won’t be lying - he’s aware of Sam’s body in the same detached kind of way he’s aware of his own - it’s the box his favorite person comes in, the wrapping that doesn’t really matter - but he can appreciate that it’s very nice wrapping. It has nice legs.

***

He leaves the skirt on the ugly floral bedspread while Sam’s showering and doesn’t stick around long enough to see his reaction, slips into the bathroom as Sam’s stepping out. He intended it as an easy out for Sam but as he’s staring at his foggy reflection in the glass, it hits him that he’s going to walk back out and find Sam wearing… a skirt. Or maybe not a skirt. Or maybe nothing but a skirt. What does he usually wear with it? They should have discussed this more. 

Sam’s standing awkwardly by the bed. His face is flaming red, hair still wet and curling around his ears and neck, bottom lip caught nervously between his teeth. He’s wearing the skirt. 

He’s also wearing a tight t shirt, too tight, something Dean’s never seen on him. It rides up a little, reveals a thin strip of flat stomach just above the top of the skirt. That fucking skirt.

It sits snug and low on his hips, tight to his body until it just barely flares out. It’s short enough that the creamy pale part of Sam’s thigh is revealed and Dean was right, his legs  _do_  look awesome like that, right down to the sheer white socks that come up to just past his knees. 

Sam shifts his weight from one foot to the other as Dean lets his eyes travel up and down, lingering on that exposed line of belly, on the way the skirt doesn’t quite sit the way it would on a girl’s hips, the way it doesn’t lie flat over the space between his legs. 

Sam wipes his palms on the pink material, smoothing it down against his thighs and drawing it tighter across that telltale bump and Dean lets out the breath he didn’t know he was holding.

“You wanna turn around, lemme see the rest?” Dean asks, making his way over to the bed. He sits back against the headboard without taking his eyes off Sam. 

Sam does it, turns slowly and as soon as he’s facing away, he squares his shoulders, arches his back a little and the back of the skirt is tight, fabric pulled taut over Sam’s ass but sticking out below it, not quite managing to follow the curve to his thighs. There’s space there, space for a hand or -

“What do you usually do now?” Dean asks when Sam’s completed his circle, eyes fixed on the carpet. 

“Dean.” There’s a new kind of whine in Sam’s voice, not his usual plaintive “Dean”. This one’s more like a plea. 

“Just tell me.” Gotta make sure Sam gets what he needs, make sure he doesn’t want to go to anyone else for this. Ever. “If you, uh, wanna. You don’t have to.”

“I - I jerk off.” If Sam turns any redder he’s going to spontaneously combust. Dean knows the feeling - there’s something burning under his skin, something ticking like a time bomb behind his ribs. 

“How?” He doesn’t know how he’s keeping his voice steady when all the air in the room is gone. “Wanna show me?”

Sam freezes for a moment, long enough for Dean’s eyes to catch on the way the front of his skirt is being pushed out. Sam nods and takes a step towards the bed, finally meeting Dean’s eye. It’s a defiant look, a dare, but underneath it Dean can see Sam’s fear like a neon sign. 

It hits him that this is brave, what Sam’s doing. This isn’t risking his internal organs, the pulse in his throat, on a hunt that might leave him mangled and bloody - this is risking Dean, risking everything they are and Dean is suddenly, ridiculously proud of Sam. For showing Dean, for trusting Dean enough to show him. 

“I do it on the bed. On my knees, pretend someone’s bending me over and…” Apparently the rest of that sentence isn’t going to make it past Sam’s clenched teeth. That’s okay, Dean can work with what he’s got. He slides off the mattress and gestures for Sam go ahead, watches as Sam kneels in the center of the bed and bends until he’s on his elbows, back arched obscenely, face hanging inches from the scratchy blanket. 

It occurs to Dean that he hasn’t been fulfilling his end of this bargain. 

“Fuck, you look good like that.” Once the words are out, it’s like something unlocks in his chest and it all comes pouring out. “Look so perfect, so fucking pretty in that little skirt, bet you’d have guys breaking the door down if they saw you.” Dean circles the bed, stands behind Sam and  _fuck_ , there’s his little brother’s perfect, bare ass. 

It’s possible this is getting a little out of hand. 

“No panties, huh Sammy?” Sam makes a little choked sound in the back of his throat and shakes his head, one hand dropping to his cock. Dean shifts until he can see it - one of Sam’s hands wrapped tight around the base, not stroking, just holding on. “Maybe next time I’ll get you some, pretty pink ones to go with that skirt. Maybe see if I can make you come in them, get them all sticky and wet.” 

Sam whimpers and his knees shift further apart, head dropping to rest against the bed while his hand starts to move on his cock, one long squeeze from the base to the tip, a quick slide of his thumb over the head before it slides back down, slick and easy now. 

Dean comes back around to get a better look at Sam’s face. Still burning pink, eyes screwed shut and lips bitten dark, parted around a series of gasps and pants that has Dean’s cock jerking against his zipper.  _Jesus._  

“Tell me what you’re thinking about.” The words are out before Dean has a chance to think them through and the second he hears them there’s a fierce surge of jealousy spiking through his veins. “You thinking about someone touching you? Pushing your skirt up and fucking you with it up around your waist?”

A little twinge of worry reminds Dean that he doesn’t actually know if Sam wants to get fucked, if that’s part of this, but Sam moans and nods against the bed, hand moving faster now, hips rocking down into his fist. 

Dean’s just starting to think Sam’s not going to answer when his eyes fly open and find Dean’s, black overtaking hazel, a desperate, reckless light in them. 

“Thinking about you,” Sam gasps and it’s a punch to the gut, the Impala cresting a hill too fast, weightless. “Your hand up my skirt, makin’ me wear it in the car, makin’ me ride you. Wanna - wanna be good for you.”

_Fuck._

“You wanna be a good boy for me? Want me to make you take it, want me to bend you over and pull your panties down, fuck you so hard you can’t sit for a week?” Dean’s mouth is completely out of his control, filth pouring out while he palms his dick  _hard_  and watches Sam, watches his body curve and arch like Dean’s actually doing it, actually fucking him.

“Fuck you’re so hot like this Sam, wearin’ that skirt for me, being so good for me.”

Sam lets out a whimper that has Dean pretty sure he’s going to come in his pants and he really doesn’t care, doesn’t even unzip his jeans because Sam looks like he’s about to lose it and Dean can’t take his eyes off him for even a second. 

“Dean - oh god - Dean, I’m gonna - “

“Yeah, c’mon Sammy, let me see you come like that,  _fuck_ , do it.”

Sam comes with a strangled moan, hand flying over his cock while the other grips the bedding, his body twisting and jerking, skirt shoved up by the movement, face screwed up in pleasure. The sight is enough to push Dean over the edge, hips shoving up against his own hand, knees nearly bucking at the pleasure drawing up through him, pulsing hot and thick into his boxers. 

He half steps and half crumples onto the bed where Sam’s lying on his side, inches from the wet puddle of come in the center. He looks… perfect, hair mussed in every direction, face still flushed red, chest heaving and skirt still rumpled up to reveal his sticky, softening cock. 

His eyes are slitted, fuzzy gaze on Dean’s face, the only hint of nervousness the way he tugs his skirt down to cover himself. 

“Was that - ” Dean starts, clears his throat -  _Jesus, he sounds like he gargled with Drano this morning._ “Was that okay?”

Sam nods and curls toward Dean, contorting his body to avoid the come, and Dean stretches out an arm to wrap it around his skinny shoulders, tugs him in closer. 

“What do you say? Panties next time?” Dean tries for playful, but they both know what he’s really asking. 

“Mmhmm. You have to buy ‘em though.”

“‘Course.” Dean grins, braces for the elbow his ribs are about to receive. “Anything for my pretty little brother.”


End file.
